600 E. Grand Ave., Navy Pier
Established in 1926, The original Rainbow Cone Location on 92nd and Western is an interesting little slice of Chicago history—it's long been the spot for family outings (and more than a few dates), and in the war years owner Joseph Sapp installed a radio so customers could get news when they stopped in. The thing to order since the early days has been their iconic rainbow cone, a pointed cake cone piled with layers of chocolate, strawberry, Palmer House (their blend of vanilla with cherries and walnuts), pistachio, and orange sherbet that tastes way, way better than it sounds. Their rainbow ice cream cakes, which include all five flavors layered on top of yellow cake, are nice for a last-minute celebration, as they always have a few on hand that can be personalized on the spot. FYI: They're only open in the summer months, and recently opened this Navy Pier location.